Poonsakdi PloypradithThaninee PetchmaneePoolsak SahakitpichanNichole D. LitvinasSomsak RuchirawatChulabhorn Research InstituteThe Institute of Science and Technology for Research and Development, Mahidol UniversityStanford University2018-08-202018-08-202006-12-08Journal of Organic Chemistry. Vol.71, No.25 (2006), 9440-9448002232632-s2.0-33845530699https://repository.li.mahidol.ac.th/handle/20.500.14594/23138(Chemical Equation Presented) Twenty-eight natural and unnatural lamellarins with either a saturated or an unsaturated D-ring were synthesized according to our developed synthetic route. The key step involved the Michael addition/ring closure (Mi-RC) of the benzyldihydroisoquinoline and α-nitrocinnamate derivatives, which provided the 2-carboethoxypyrrole intermediates in moderate to good yields (up to 78% yield). Subsequent hydrogenolysis/lactonization furnished lamellarins with a saturated D-ring in excellent yields (up to 93% yield). DDQ oxidation of the saturated lamellarin acetates led directly to the corresponding unsaturated analogues in 54-95% yield. In addition, only two steps in our developed strategy require column chromatography. © 2006 American Chemical Society.Mahidol UniversityChemistryArticleSCOPUS10.1021/jo061810h